15647-43-5

Basic information

• Product Name: N^δ-benzoyl-L-ornithine
• Synonyms: N^δ-benzoyl-L-ornithine
• CAS NO: 15647-43-5
• Molecular Weight: 236.271
• Mol File: 15647-43-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: N^δ-benzoyl-L-ornithine(CAS DataBase Reference)
• NIST Chemistry Reference: N^δ-benzoyl-L-ornithine(15647-43-5)
• EPA Substance Registry System: N^δ-benzoyl-L-ornithine(15647-43-5)

Safety Data

• Hazardous Substances Data: 15647-43-5(Hazardous Substances Data)

Upstream product

• 150211-24-8 Boc-Orn(Bz)-OH 

Downstream Products

• 880145-14-2 N⁵-benzoyl-N²-(toluene-4-sulfonyl)-L-ornithine 
• 900497-71-4 N⁵-benzoyl-N²-methyl-N²-(toluene-4-sulfonyl)-L-ornithine 
• 15647-44-6 N⁵-benzoyl-D-ornithine 
• 16748-29-1 N^α-Methyl-L-ornithin 
• 54907-87-8 (S)-5-benzoylamino-2-bromo-valeric acid 

Relevant articles and documents

The Effects of Prodrug Size and a Carbonyl Linker on l-Type Amino Acid Transporter 1-Targeted Cellular and Brain Uptake

The l-type amino acid transporter 1 (LAT1, SLC7A5) imports dietary amino acids and amino acid drugs (e. g., l-DOPA) into the brain, and plays a role in cancer metabolism. Though there have been numerous reports of LAT1-targeted amino acid-drug conjugates (prodrugs), identifying the structural determinants to enhance substrate activity has been challenging. In this work, we investigated the position and orientation of a carbonyl group in linking hydrophobic moieties including the anti-inflammatory drug ketoprofen to l-tyrosine and l-phenylalanine. We found that esters of meta-carboxyl l-phenylalanine had better LAT1 transport rates than the corresponding acylated l-tyrosine analogues. However, as the size of the hydrophobic moiety increased, we observed a decrease in LAT1 transport rate with a concomitant increase in potency of inhibition. Our results have important implications for designing amino acid prodrugs that target LAT1 at the blood-brain barrier or on cancer cells.